Ammonia → (2-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethynyl)triisopropylsilane

HRID 2106416

Reaktionsgleichung

Reaktionsgleichung von HRID 2106416
C([Mg]Cl)(C)C.I[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.C([Cu])#N.[Li+].[Cl-].[Br:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38]Br)[CH:32]=1.[Cl-].[NH4+].N>O1CCCC1.O>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH:32]=1)[CH2:38][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1

Komponenten

10

Edukt 7

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 433294Lithium Chloride2×HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzeneHCID 57809611((4-Iodophenyl)ethynyl)triisopropylsilaneHCID 178418546HCID 178418546, Verbindung2×HCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 16065644(2-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethynyl)triisopropylsilane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

Under argon 0.66 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran are added dropwise to a solution of 0.50 g (4-iodo-phenylethynyl)-triisopropyl-silane in 2.2 ml dry tetrahydrofuran chilled to −25° C. The solution is stirred for 30 min at −25° C. and then combined with 0.26 ml of a 1 M solution of CuCN*2 LiCl in tetrahydrofuran (prepared by dissolving CuCN and LiCl in the ratio 1:2). Shortly afterwards, 0.35 g 4-bromo-2-bromomethyl-1-chlorbenzene are added and the reaction mixture is brought up to −5° C. in the cooling bath. After 6 h stirring at −5° C. the solution is heated to ambient temperature and stirred overnight. Then a mixture of saturated ammonium chloride solution and 25% ammonia solution (9:1) is added and the resulting mixture is added to water. The organic phase is separated off and the aqueous phase is extracted with ethyl acetate, the combined organic phases are dried over sodium sulphate, and the solvent is removed. The residue is purified through silica gel (cyclohexane).

Aufarbeitung

  1. customprepared
  2. customis brought up to −5° C. in the cooling bath
  3. stirringAfter 6 h stirring at −5° C. the solution
  4. temperatureis heated to ambient temperature
  5. stirringstirred overnight
  6. additionis added
  7. customThe organic phase is separated off
  8. extractionthe aqueous phase is extracted with ethyl acetate
  9. dry with materialthe combined organic phases are dried over sodium sulphate
  10. customthe solvent is removed
  11. customThe residue is purified through silica gel (cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-6049f4a0dc1c463aa0e9ab5514eae38c
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579449B2

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